108-28-1Relevant articles and documents
Deoxyribonolactone formation in photoirradiation of 5-bromouracil-containing oligonucleotides by direct C1′ hydrogen abstraction
Fujimoto, Kenzo,Ikeda, Yutaka,Ishihara, Shigenori,Saito, Isao
, p. 2243 - 2245 (2002)
Mechanistic studies on the formation of deoxyribonolactone by UV irradiation of hexamer d(GC1BrUGC)2 (ODN 2a) containing 1′-deuterio-2′-deoxyadenosine 1 was examined. The kinetic isotope effect (kH/kD) for the f
HETEROORGANIC FURAN DERIVATIVES. 61. TRIMETHYL(5-METHYL-2-FURYL)SILANE AND TRIMETHYL(5-METHYL-2-FURYL)GERMANE
Lukevits, E.,Ignatovich, L. M.,Iovel', I. G.,Gol'dberg, Yu. Sh.,Shimanskaya, M. V.
, p. 15 - 17 (1987)
The transformations of trimethyl(5-methyl-2-furyl)silane and trimethyl(5-methyl-2-furyl)germane were studied upon vapor-phase oxidation by atmospheric oxygen on a V-Mo-Ag-O catalyst.Under these conditions, trimethyl(5-formyl-2-furyl)silane and trimethyl(5-formyl-2-furyl)germane are formed albeit in only 5-7percent yield.This low yield is a consequence of the thermal instability of the starting compounds and the aldehydes formed.The oxidation of 2-methyl-5-tert-butylfuran was studied under comparable conditions.The corresponding aldehyde was obtained in 30percent yield.A scheme was proposed for the catalytic oxidation of 5-substituted 2-methylfurans.
A palladium catalyzed efficient synthesis of γ-methylene-α, β-unsaturated γ-lactones via cyclization of 3,4-alkadienoic acids
Ma, Shengming,Yu, Fei
, p. 9896 - 9901 (2005)
An efficient method was developed for the synthesis of γ-methylene- α,β-unsaturated γ-lactones from the Pd-catalyzed cyclization of 3,4-alkadienoic acids. Control experiment shows that the reaction should be carried out under a N2 atmosphere to ensure the high purity of the products.
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Shaw
, p. 2510,2512 (1946)
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Pd/C-Cu mediated direct and one-pot synthesis of γ-ylidene butenolides
Rambabu,Bhavani,Nalivela, Kumara Swamy,Mukherjee, Soumita,Rao, M.V. Basaveswara,Pal, Manojit
, p. 2151 - 2155 (2013)
10% Pd/C in combination with CuI, PPh3, and Et3N has been identified as an effective catalyst system for the coupling of (Z)-3-iodoacrylic acid with terminal alkynes in 1,4-dioxane leading to the one-pot synthesis of γ-ylidene butenolides. The methodology showed remarkable regio- and stereoselectivity as only the five-membered lactone ring products were formed with an exocyclic double bond possessing Z-geometry.
Intramolecular Photocycloaddition of 2(5 H)-Furanones to Temporarily Tethered Terminal Alkenes as a Stereoselective Source of Enantiomerically Pure Polyfunctionalyzed Cyclobutanes
Xin, Yangchun,Rodríguez-Santiago, Luís,Sodupe, Mariona,álvarez-Larena, Angel,Busqué, Félix,Alibés, Ramon
, p. 3188 - 3199 (2018)
Allyloxymethyloxymethyl and 4-pentenoyloxymethyl substituents have been used as tethering groups to study the intramolecular [2 + 2] photocycloaddition of chiral 5-substituted 2(5H)-furanones. The photoreactions proceed in good yield and provide the expected regio- and diastereoselective tricyclic compounds with complementary regioselectivity, which depends on whether the vinyl chain is attached to the furanone by an acetal or an ester linkage. Computational simulations agree with experimental observations and indicate that the origin of the different observed regioselectivity in the intramolecular photochemical reaction of lactones 5 and 6 arises from the relative stability of the initial conformers. The synthetic potential of the enantiomerically pure photoadducts is illustrated by preparing an all-cis 1,2,3-trisubstituted cyclobutane bearing fully orthogonally protected hydroxyl groups.
Efficacy and site specificity of hydrogen abstraction from DNA 2-deoxyribose by carbonate radicals
Roginskaya, Marina,Moore,Ampadu-Boateng,Razskazovskiy
, p. 1431 - 1437 (2015)
The carbonate radical anion CO3?- is a potent reactive oxygen species (ROS) produced in vivo through enzymatic one-electron oxidation of bicarbonate or, mostly, via the reaction of CO2 with peroxynitrite. Due to the vitally essential role of the carbon dioxide/bicarbonate buffer system in regulation of physiological pH, CO3?- is arguably one of the most important ROS in biological systems. So far, the studies of reactions of CO3?- with DNA have been focused on the pathways initiated by oxidation of guanines in DNA. In this study, low-molecular products of attack of CO3?- on the sugar-phosphate backbone in vitro were analyzed by reversed phase HPLC. The selectivity of damage in double-stranded DNA (dsDNA) was found to follow the same pattern C4′ > C1′ > C5′ for both CO3?- and the hydroxyl radical, though the relative contribution of the C1′ damage induced by CO3?- is substantially higher. In single-stranded DNA (ssDNA) oxidation at C1′ by CO3?- prevails over all other sugar damages. An approximately 2000-fold preference for 8-oxoguanine (8oxoG) formation over sugar damage found in our study identifies CO3?- primarily as a one-electron oxidant with fairly low reactivity toward the sugar-phosphate backbone.
THERMAL ANALYSIS OF 1-DEOXY-1-GLYCINO-D-FRUCTOSE AND 1-β-ALANINO-1-DEOXY-D-FRUCTOSE
Birch, Edward J.,Lelievre, John,Richards, Edward L.
, p. 263 - 272 (1980)
Aspects of the pyrolysis of 1-deoxy-1-glycino-D-fructose and 1-β-alanino-1-deoxy-D-fructose are reported.Thermal analysis and parallel chemical investigations demonstrate that formation of these Amadori compounds provides a low-energy route to the thermal degradation of their amino acid and sugar moieties.Furthermore, the pathway leads to the production of increased quantities of various aroma compounds as compared with controls.Pyrolysis of the 1-amino-1-deoxyketoses also produces the toxic compound protoanemonin; a degradation pathway leading to its formation is proposed.